Hydrogen Bromide → (+)-5,6-Dimethoxy-2-[2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-yl]isoindoline hydrobromide

HRID 2211732

Reaktionsgleichung

Reaktionsgleichung von HRID 2211732
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[CH2:8][N:7]([C:14]1[C:15]([CH3:34])=[C:16]([CH3:33])[C:17]3[O:21][C:20]([CH3:23])([CH3:22])[CH:19]([C:24]4[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=4)[C:18]=3[C:31]=1[CH3:32])[CH2:6]2.[BrH:35]>C(O)(=O)C>[BrH:35].[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[CH2:8][N:7]([C:14]1[C:15]([CH3:34])=[C:16]([CH3:33])[C:17]3[O:21][C:20]([CH3:23])([CH3:22])[CH:19]([C:24]4[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=4)[C:18]=3[C:31]=1[CH3:32])[CH2:6]2

Komponenten

4

Edukt 2

HCID 260Hydrogen BromideHCID 99119865,6-Dimethoxy-2-[2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-yl]isoindoline

Produkt 1

HCID 21961319(+)-5,6-Dimethoxy-2-[2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-yl]isoindoline hydrobromideAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

(+)-5,6-Dimethoxy-2-[2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-yl]isoindoline (150 mg, 0.327 mmol) was dissolved into a 25% solution of hydrogen bromide in acetic acid and the mixture was concentrated under reduced pressure. The residue was crystallized from methanol to obtain 92 mg (52% yield) of the title compound. Melting point: 174-177° C. [α]D=+40.2° (c=0.495, methanol).

Aufarbeitung

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customThe residue was crystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-ee5c98db8d584364a5853bf348d168ad
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07101867B2

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